


Evil Author Day: "An Evening With El Diablo"

by PassionPhantom



Category: Supernatural
Genre: Anal Fingering, Anal Play, Castiel & Meg Masters Friendship, Dead Dove: Do Not Eat, Demon Dean Winchester, Dry Orgasm, Evil Author Day 2020, F/F, F/M, Forced Ejaculation, Forced Orgasms, Human Castiel (Supernatural), Hurt No Comfort, M/M, Multiple Orgasms, Orgasm Control, Orgasm Delay/Denial, Rape, Rape/Non-con Elements, Rough Sex, Vibrators, Violence, Voyeurism, fuck machines
Language: English
Status: Completed
Published: 2020-02-15
Updated: 2020-02-15
Packaged: 2021-02-26 12:16:09
Rating: Explicit
Warnings: Graphic Depictions Of Violence, Rape/Non-Con
Chapters: 1
Words: 3,415
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22741312
Author URL: https://archiveofourown.org/users/PassionPhantom/pseuds/PassionPhantom
Summary: ***EVIL AUTHOR DAY 2020***Quiet, shy and alone in the world, Cas decides to give love a try. He meets a mysterious yet friendly man at a coffee shop and Cas instantly falls in love with him in just a matter of days.Without knowing what kind of monster Dean Winchester really is.
Relationships: Castiel & Dean Winchester, Castiel/Dean Winchester
Comments: 5
Kudos: 31





	Evil Author Day: "An Evening With El Diablo"

**Author's Note:**

> Something that was once intended for the Dark SPN Bang 2019 but was left unfinished but not forgotten.
> 
> I’ve got the whole story outlined. But I just can’t seem to write it.

Cas screams out of his troubled slumber as another nightmare forces him to wake. He looked around the large bedroom and realized that Dean had carried him from the couch to the bed. 

“Dean?” Cas called out but there wasn’t any answer and safely enough, Castiel assumed that Dean was gone to grab dinner. Until he looked at the clock on the nightstand and noticed that it was nearly midnight. The witching hour. Dry mouthed and shaking from his hellish dream, Cas got up and walked around the older man’s house.

The tv in the living room was still on and the lights were dimmed down, like usual. Castiel sighed. 

‘Maybe he went back to the office.’ Castiel innocently thought and moved about the house. Helping himself to something to drink in the kitchen, turning off the television in the living area and slowly moving back to the bedroom to get more sleep. 

That when he hears a loud sound coming from the basement. It was terrifying and continuous as it consisted of wild thuds and shrieking. Like metal being dragged against the floor. The lights flickered back on in the house as the clock struck midnight. Castiel was already freaked out about his nightmare and this shit didn’t help. He always knew that he was haunted somehow… he just thought he was safe from his demons after meeting his beloved Dean. 

“Dean!” Cas called out as he slowly began to move toward the basement entrance. There was another loud bang...Cas flinches and doesn’t realize he no longer has control over his body. His feet begin to foolishly move toward the loud banging. 

_ Dean had always warned his little sweet Castiel to never go to the basement... _

When Cas finally reached the bottom of the stairs, Castiel shakily flips on the light switch. Ignoring the rule Dean told him in the past to never come down there. Castiel thought he’d be ready and in his defense he was scared...but as the lights came on his big blue eyes widened in confusion as he saw all of what he saw. 

Yet, before Castiel could take it all in, Dean Winchester steps around the dark corner and said, “Well, it’s about fucking time,” before knocking Castiel out.

* * *

  
Castiel groaned deeply as he woke up. Everything was foggy and he felt disoriented as he tried to move. But he couldn't. It took Cas a while to notice the position he was in and the young man whimpered as he realized that he was lying face down naked on a cold table with his backside in the air. 

He could taste the leather of the ball gag in his mouth and his wrists were cuffed underneath him; painfully connected to his ankles with shackles. Cas tried to move, but his body was locked into position through the hooks on the stainless steel table. He couldn’t turn around to see that he was angled in front of a large machine.

“You’re awake, good.” Dean turned from his desk of ‘supplies’ and stepped over to the table Cas was on with a crystalized bottle of lube in his free hand. 

Dean touched Castiel’s backside gently and felt the younger man flinch terribly. 

“I thought I was going to have to wake you abruptly with my ‘Little Friend.’”Dean chuckled lightly. 

Castiel's eyes grew wide in confusion and he longed for Dean to stop whatever he was trying to do. Questions raged through Castiel’s mind and he muffled against his gag as he became absolutely terrified. 

Dean grinned devilishly at the sight of his lover and got to work. The man was beyond thrilled to get started and by the way, his dick was growing hard, he knew that he would not have much patience. 

The machine Castiel was propped in front of, was wide and made with stainless steel. It was a monstrous thing with various settings and a massive crimson-colored dildo on its receiving end. The redden toy was hard and also had veins protruding all over its girth. 

Grabbing hold of the fake cock, Dean opened the exquisite bottle of lube with his teeth than spat the top out of his mouth. The thick glass object hit the floor with a thud and Castiel’s limbs attempted to flinch at the sound. Dean ignored his little movements and continued to labor on. 

Carefully, the handsome man poured the thick liquid over the toy generously. Drenching it until it was dripping and covered entirely in a glossy wet sheen. Then he turned his attention to Castiel’s quivering backside. He slapped it viciously and laughed at the sound of Castiel’s muffled cries. 

This was his way of being kind, in a strange way. Dean applied the lube all over Castiel’s ass cheeks until his flesh was glimmering in it. Dean bit down on his bottom lip, savoring the sight of Cas before opening his entrance and pouring the rest of the lube over his muscle. 

Castiel sobbed and couldn't believe what was happening to him as he felt the warming liquid pour over his skin and his hole. He didn’t realize that his entrance was twitching and he definitely didn't have knowledge of how the involuntary action made Dean swell with a dark lust. 

Dean slapped Cas’ ass again, digging his nails into his skin roughly. 

“Such a sweet ass, Castiel. . . I’m going to enjoy training you. I really am, sweetheart.” Dean laughed sadistically. “We’re going to have a little fun, Lover.” 

Dean was savagely hard now and he was beyond ready to have Cas’ body all to himself. Still, he slowed himself down while grabbing hold of the red dildo and positioned it closer to Cas’ entrance. Guiding it through carefully and slowly pushing the thick head of it through Cas’ hole. 

Castiel's eyes widened and rolled into the back of his head. His hole opened and was stretched out furiously wide just by the head of the dick. Cas squirmed his backside, trying to pointlessly get it out of him. Hoping it would just fall out from being too slippery. He shrieked out a dull scream as Dean pushed it in further. 

“Aw, Right there should be good enough, darling.” Dean smiled and kissed Cas’ trembling ass before heading to the other side of the basement. He grabbed the little black remote control for the sex machine and scoffed, 

“I have been aching to use this on you. Let’s see how you like it, shall we?”

Castiel sobbed and tried to shake his head. 

Dean ignored his pleading and pressed the lower button. 

All of the muscles in Castiel’s body tensed up as the machine started to awaken. The slippery dildo moved in and out at a slow pace. Stretching Cas’ hole and slicking against his walls. The veins on it massaged his insides and Cas felt his toes curl suddenly. 

Eyes watering and his gagged mouth dripping saliva through the ball, Cas felt the sensations build up inside him. Confused and scared, he had no time to think about why Dean would do this anymore. It was happening. That was all he could think about and as the machine pumped him so slowly Castiel moaned filthily. A strange pleasure increased inside him and he rolled his hips, mindlessly.

Dean listened to the moans and smiled and allowed Castiel to _ ‘enjoy’ _ the fuck machine. The dominant man watched and walked around the table as Castiel twisted and squirmed his hips. The younger man’s body bucking up and rocking back and forth to meet the long deep strokes.

Dean knelt in front of the table and studied Cas’ deep red face. Castiel shook his head and felt the tears stung his eyes, blinding him. Dean bent down, pressing their foreheads together. 

“Just relax and let it make you feel good,” Dean said with a devilishly grin. Then he took the remote and pressed the middle button.

The dildo pumped faster and thickly. Cas’ stomach heaved and his heart raced. His limbs went numb. His widened thighs trembled and his wrist and ankles ached for release. Yet, a gush of pleasure rushed through him and went straight to the very tip of his own hardening cock. 

Lost in it, Cas was trapped. He had no choice but to endure the feeling of the dildo inside pumping him. He didn’t understand what was happening. The shock ran through his nerves and exploded in his body as he dug his teeth into the ball gag. 

‘Why is Dean doing this to me?’ Castiel asked himself as he tried to sob, move and cry. The confusion twisted into Cas’ mind continuously and he felt a strange gulit eat at his heart as his own cock swell. It was as if he was participating in his own assault and he couldn't comprehend how Dean, his boyfriend could be enjoying this. 

‘I thought he loved me. Why? How could this be happening?’

“How about we speed things up a bit,” Dean said, standing up now and pressing the remote’s top button. 

The machine hummed louder and the hydraulics shook. The dildo shot its way in and out at a rapid-fire speed, stabbing at Cas’ insides. Dean laughed demonically, watching as Cas’ eyes rolled back again and nothing but the whites were showing. 

The devious man licked his lips and saw how Cas’ entire body was dripping wet with sweat. His hair was dripping and his back muscles were twitching. 

It was too much. The heat built up in Cas’ body and sent him overboard. But it was nothing compared to what Dean was about to do next. 

Pressing the side buttons, Dean started the vibration and rotating options and from there on Castiel roared anew. The room spun around and went dark as Cas fading in and out of his consciousness. It only lasted for five seconds before everything went completely black. 

Stopping the machine, Dean tossed the remote to the side of the table. Studying Castiel’s limp body. Caressing his hair and whispering torments to him while listening to the delicate sounds of Castiel whimpering in his daze. Dean allowed Cas to rest and come back to reality slowly. 

Dean made himself busy with taking the dildo out of Cas and wheeling the sex machine to the other side of the torture chamber. He cleaned up everything until he could barely handle the raging lust inside him. His cock was throbbing hard against the fabric of his pants. Dean bit his lip and unzipped his pants. Stepping out of them while taking off his shirt, he licked his lips then made his way over to Cas. 

Without hesitation, he took hold of his victim’s hips and plunged his cock deep inside Cas’ hole--waking Castiel up. 

Cas eyes opened but he was blinded by heavy tears. Shrieks and screams ached to release from his throat but he held back his sounds. It was pointless. 

Dean gritted his teeth and thrust in deep slow strokes. Aiming for Cas’ prostate. His own mouth watering as he felt the younger man’s wetness and relishing in a wicked bliss as he took what he wanted. 

* * *

**2 weeks later**

* * *

“Aww let’s play with this lovely ass.” Gunner said and Castiel flinched and cried out as he felt the man’s lube slicked fingers tickle at his hole.

“No no no, please, don’t,” Cas begged and was devastated when the men laughed and Gunner shoved his fingers inside. Going straight for Cas’ prostate. 

Castiel’s hips shot off the bed as he tried to escape it, but Neil held him down, while the other man, grabbed Cas’ cock and spat all over it, and Gunner played with Cas’ g-spot. 

“NO! STOP IT!” Castiel cried out and thrashed around. Feeling everyone’s hands on him. Pressure built up as his own cock was jerked and prostate massaged at a ferociously evil speed. His balls twitched and the room began to spin as waves of unwanted pleasure began to hit him. 

“Awww!” Castiel moaned and felt his body react on its own. His legs grew wide and his hips starting rocking back and forth in cadence to the movements. 

There was laughter and encouragement from the group of men and Cas regretted the moans that were escaping from him. But it all started to feel so good. 

“Oh my God! Awww!” Castiel’s eyes opened as he suddenly felt two wet hot tongues begin to battle over his cock head. Flicking at his tip, Running down his hardened shaft, tracing over the veins forming on it and then eventually sucking on his balls. 

Then another one of Dean’s men came over and applied his wet tongue to Cas’ tip. Castiel swore to himself he was in hell but he was seeing heaven as the third guy swirled his tongue on his slit in circular motions. 

The evil son of a bitch, Gunner, was still at in on Cas’ g-spot and in the middle of it, all Castiel felt a rhythmic sensation. Gunner finger fucked him in circles, the man tonguing his slit did so in circles, and the guys sucking on each of his balls were humming swirling their tongues over the skin...in circles. 

It was ecstasy and Cas was almost driven insane by it. He knew that if he didn't come soon he was going to go insane.

“Oh God, Please! Please! Just make me come already! Please!” Castiel begged his rapists. There was an uproar of laughter and cheer from the group and Cas’ heart broke into pieces as they all suddenly stopped the activity to laugh at him.

He cried and heard the group shuffling around and talking amongst themselves. 

“Let me have my turn.” Another guy said with an eager tone. 

Someone came and took hold of Castiel’s ass and spread his cheeks wide open. 

“AH!” Cas jumped and screamed as a hard cock teased his hole.

Cas’ pupils dilated as the man pushed his way inside slowly. Stretching Cas out and making his hips squirm. Inflamed with pleasure from the stretch, Castiel moaned miserably and trembled.

* * *

Dean watched Castiel’s assault as the other three women worked over his cock. The chamber was full of screams and moans and the space grew hot as Hell itself as everyone moved. 

Meg had started to suck Dean’s cock but she heard the newcomer’s screaming and she turned around and shivered. Dean noticed this immediately and reached down to slap Meg. 

“Come sit on this dick, now.” The demon King ordered and the woman obeyed. Ruby and Anna moved out of the way while Meg stood up, turned around, and sat on Dean’s lap. She looked down trying to avoid the horrific rape occurring; trying to ignore the screams and cries. Dean noticed and quickly struck the back of her head and snarled, 

“Watch it.” He pulled on her long brown hair and brought her face up, forcing her to see it all. 

Castiel’s screams were suddenly muffled as Gunner and Jared tried to shove both of their cocks into Cas’ mouth at the same time. They laughed and Meg watched as the two men fought over Castiel’s lips. Slapping their cocks over his sweat covered face and battled playfully for dominance.

Jared eventually pushed Gunner to the side abruptly and was ultimately the winner as he dicked his way into Cas’ throat and started to fuck. 

All the while, Neil had been slamming into Cas’ backside mercilessly as the other guy, David helped by holding open Castiel’s cheeks and spitting his hole. Blood ran down Cas’ legs profusely as his rectum was being ripped. 

Meg gasped when she saw the blood. 

“That’s right girl, watch all of it.” Dean laughed than kicked Meg’s legs open and angled her hips before pushing himself inside her. Meg kept quiet, biting back her own want to shout, and she fixed her eyes on the men gang-raping Cas. Listening to the sounds of devious laughter, squeals, and wet skin clapping, Meg started to move her hips slowly like a proper slave to her demonic king.

Castiel cried out miserably just as Dean sat up to whisper in Meg’s ear, 

“You like the sound of him, don’t you? Does it make you want to help poor little Cas?” The demon king played with her hair and Meg rolled her eyes. Dean grew bored when she didn’t answer. 

The king snapped his fingers then ordered Ruby and Anna to come over. 

"Anna, rub her clit. I want her to be wetter than this. Ruby come over here and give her tits some attention." 

The two got started without hesitation. Dean pulled Meg backward--flushing her body against his hard chest as the other girls got to work. 

Ruby took hold of one of Meg’s breasts as she started to lick and suck on the other. The warmth of Ruby’s little tongue darted over Meg’s nipple and she squirmed. 

Anna settled herself in between Meg’s thighs and sucked on her fingers quickly before slipping them in between the other woman’s labia. Spreading the swollen lips, Anna began to flick Meg’s clit softly. Too softly. 

Meg flinched at the sudden build-up of heat as Anna teased and rubbed her. It was not their first time assigned to each other at all and Meg knew that Anna had skills on what to do to another woman. The former angel knew the exact amount of pressure to apply and the exact speed to go in order to make Meg come. And it didn't take long for Meg’s vaginal muscles to contract brutishly around The Dark King’s girth.

“Aww!” Meg’s involuntarily moans blended in with Castiel’s sobbing. 

The room was loud with it and Dean laughed devilishly feeling as Meg came over his cock. Feeling her grow wetter, Dean started to fuck her. 

“That’s right girl, go ahead and listen to that shit.” He taunted in Meg’s ear. “Listen to his squeals. Listen as my boy’s fuck him like a whore.” Dean ran his hand down Meg’s torso and rutted her. “Imagine if you were the one giving it to him, dominating sweet little Castiel. Imagine if he was at your mercy, begging you to stop. Imagine if you had that power.” 

Meg shook her head and squeezed her eyes shut. She tried to deny how good it felt. The taunting was terrifying, Dean was terrifying. But soon she gave up and allowed herself to feel all that her master whispered to her. 

She grew wetter, moaned louder and felt powerful as if she was no longer a slave. As if she were the dominant one, taking all she wanted. Letting Dean fuck into her, Meg held her legs wider and shuddered. Despite being a horrid creature, Dean knew how to use his cock and he pumped and rolled his hips. Hitting every sweet spot he could find. 

Moaning and squirming, Meg listened to Cas’ pleas in the background. Anna was still working on her clit and Ruby was now sucking on her breast. Meg gave into the _ power _Dean was whispering about and she felt a guilt surge through her but also a dark pleasure that made her body swell. 

“AW! FUCK, FUCK!” Meg came again and again until she lost her mind. 

“That’s right, come on this dick,” Dean pulled her hair and hissed. Thrusting into her and relishing as she clenched up around his hard cock again. The slippery wetness silking over him. Dean was ready to release inside her. 

But he pulled out and pushed her off of him. Meg landed on the floor and turned around to see the monster of a king take hold of Anna and force her head down to his lap. 

Mindless and dead inside, Anna sucked on her king and shook a little as Dean burst his load inside her mouth. She swallowed and bobbed her head until the King gripped her red hair and pulled her off.

On the other side of the room, Castiel's brutal rape came to a halt as all the men involved gathered around and released on him. 

Castiel laid on the floor barely breathing as he felt their come splattering on his back, his legs, his face and in his hair. He listened to their laughter and felt as Neil slapped his ass one last time. Cas lied still quietly and listened as everyone - except Dean- left out the chamber. 

The door slammed shut and Castiel blacked out. 

**Author's Note:**

> T n T sorry everyone


End file.
